A Peek into the Digital Workplace

I had the opportunity to sit down recently with fellow author Scott Berkun to talk with him about his new book The Year Without Pants, which catalogs his experience in two years with Automattic, the company that runs WordPress.com.

Our conversation touched on many different topics including innovation, collaboration, and organizational behavior.

For those of you who haven’t read the book or who aren’t familiar with how Automattic runs as an organization, here are some of the highlights:

All of the staff used to report to Matt Mullenweg, the 29-year-old creator of WordPress and founder of Automattic

When they passed 50 or so employees, about the time Scott Berkun joined, they introduced team leads

Organizational changes happen organically in the company, primarily when the pain gets great enough to force change

Automattic now has about 200 employees

Email is not the company communications standard – instead they use IRC and Skype and WordPress

Employees can work wherever they want

They have a company headquarters in San Francisco, but very few people work there

All employees get together in person annually and teams get together maybe twice in person to recharge intangibles

Hiring decisions are made not with traditional in-person interviews, but instead primarily by evaluating test projects

All new employees spend a couple of weeks working in support before occupying their intended role

Scott during his two years at Automattic led the Social team for WordPress.com and one of the things that he focused on while he was there, and that the book focuses on, is experimentation. One of the things that was fascinating in his detailing of his experience was that there was little resistance in his team to all of the experimentation that they engaged in. His theory was that they were ‘makers’ (he led a team of developers) and so they didn’t feel that there was a need to justify their existence. We spoke a great deal about why the culture at Automattic might be so accepting of experimentation, where other organizations are not, and this led to a discussion of some of my theories about the effects of scarcity and lack of firm growth, and we arrived at some of Scott’s comments that focused on the fact that there is too much fear in most organization and most managers don’t invest much time or effort in actually managing. Most managers don’t work to impact the feelings or environment for employees in companies that aren’t growing and/or where job opportunities are scarce. We then dug more into the culture topic.

Changing Culture is Painful

When it comes to culture change, there are a lot of consultants out there that would have you believe that they can come in an change your culture in 30-90 days, and while this might be possible it wouldn’t come without a great deal more pain than most organizations would be willing to bear. The reason a great deal of pain is required to affect culture change is the fact that an organization’s culture is typically determined by:

The organizations cultural history and inertia

The prevalent culture comes from the things that the largest number of people reinforce

So, in most cases changing the culture will require you to stop reinforcing behaviors that are reinforcing the current culture and start reinforcing behaviors that will lead you in the direction of the culture change you desire. What will this mean for the organization? Half the organization might leave! Are you ready for that? Many people who felt comfortable in the old culture, or that derived their power source from their old behaviors will need to be asked to leave the organization, or hopefully, will leave by their own efforts. Add into this potential chaos the fact that in most organizations the culture problem is often being created by the person asking for the culture change consulting, and how many consultants will reveal and stand behind this fact if it occurs?

One of the ways to ensure a healthy culture is constant experimentation driven by experiments that are instrumented for learning and dedicated to its pursuit. If an organization commits itself to a continuous practice of testing and learning within its management practices, in the same way that it hopefully dedicates itself to testing and learning with its products and services, then it has a much greater chance of maintaining a healthy, productive cultural environment. On the flip side, the way that we promote people in most organizations undermines the existence of a healthy, functional culture and so we need to rethink promotion. We need to ensure amongst other things that people with technical proficiency have a career path towards greater compensation that doesn’t have to include management responsibilities for those that don’t embrace the challenge and willingness to experiment in their management approaches. One of the reasons that Automattic’s culture is so strong, is because it was built to be entrepreneurial, collegial, and collaborative, and people are trusted to do what they do well (in their own way).

Of course I had to ask if people had left Automattic, and yes they have. In most cases the left to join other startups, and Scott believes that Automattic will probably stay in their minds one of the best places they worked.

Pressures From Outside

Another topic we touched on in our interview was whether or not Automattic felt pressure to make money faster after taking some VC rounds, but Scott said that while Automattic took some investment from VC’s, it was already profitable at the time and didn’t need the money but took the financing to gain other benefits and wasn’t under undue outside influence. As a result, Matt was able to purposely not assign a team or an individual to focus on growing revenue every quarter. he wanted to be careful not to turn up the monetization dial too fast because in doing so you often make bad decisions by doing so (product, etc.). There was no Store team when Scott joined, but there is now. Matt and team are very careful to maintain a long-term focus and they could easily monetize the 8th most popular web site more than they are (that’s a valuable asset), but are being careful in how they go about it.

Another thing I asked about was the impact on WordPress.com of things like Tumblr and Instagram and others, and Scott said that despite a lot of other companies and supposed competitors that have come along that have been hypothesized to supplant WordPress, they’ve never been super concerned. The reason?

WordPress itself is very flexible and so people are able to easily create themes that replicate the look and feel of a lot of the supposed competitors. The large WordPress community will build Tumblr like themes, etc. And the company itself is very resilient, and so when something new comes out, people will have a look at it and will either incorporate some of what they learn from it or ignore it if there doesn’t seem to be anything there. And, another point on the Automattic culture, if someone were to say “someone should…” in relation to something they see outside, then typically that person becomes the person to take it on.

There is a lot more I think we can learn from the Automattic experiment, and I may talk to Scott again to explore some of the learnings in the second half of the book, but wanted to rush these thoughts and nuggets from the conversation out to you. I hope they have been good for thought and you’ll think more if you’re a manager about what experiments you might run to see if you can make your group function even better.

Final Thoughts

Team size and how the organization grows up around its founder make a huge difference in how the culture evolves and reacts to its environment, and in Automattic Scott’s team was four when he started and nine when he left. The Theme team had 15 people on it, and the Happiness team (aka customer support) was the largest team at 25 people. One thing that happened along the way was when Scott’s Social team reached eight people it sort of naturally started to evolve into two separate sub-teams, which they called squads. Squad leadership was informal. There were no raises or title changes, and the squad leaders had naturally earned the most authority. They actually tried rotating leadership, but the results were mixed at best.

Another thing I asked Scott Berkun about team size was whether he thought the loose oversight and team structure would scale well as Automattic grows. He feels that it if they were to grow from say 200 to 1,000 employees they would probably insert another layer of management and break into groups of 100-150 people centered around product unit owners with teams underneath. This reinforces the thinking that they have at WL Gore, where they consciously spawn a new organization when it passes 60-70 people if my memory serves me correctly.

Wait! Before you go…

Braden Kelley is a popular innovation speaker, embeds innovation across the organization with innovation training, and builds B2B pull marketing strategies that drive increased revenue, visibility and inbound sales leads. He is currently advising an early-stage fashion startup making jewelry for your hair and is the author of Stoking Your Innovation Bonfire from John Wiley & Sons. He tweets from @innovate.